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Spain
What to Wear in Italy
In Italy, style is part of the experience. Plan to dress up more than you think you need to, keep it effortless and polished, and save the athleisure for the flight. Shop my Italy-ready favorites below.
Spain
Spain
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FAQs & Tips
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- 01This is not the time to bring every necklace you own. Pack the pieces you reach for constantly, the ones that make outfits feel finished without requiring too much thought.
- 02Book the hotel, villa, or apartment early, especially in popular cities, beach towns, wine regions, and places with limited inventory.
- 03Many of the best wineries require reservations, even when they look casual.
- 04Build the trip around a market, wine region, restaurant, cooking class, tasting crawl, or signature local dish.
- 05Comfort is key, but overly sloppy outfits can feel out of place fast.
- 06It is meant to ease you into the evening, not replace the whole night.
- 07A blazer, silk scarf, statement earrings, polished flat, or beautiful bag can make simple outfits feel dinner-ready. You do not need more clothes. You need a few pieces that make the clothes work harder.
- 08Usually, only a small amount. In most cases, withdrawing local currency from a bank ATM after arrival is the better move.
- 09A great dress, tailored trousers, linen shirt, polished tee, chic flat, or simple sandal can solve almost any travel wardrobe question.
- 10Everything takes longer with a family, so build in extra time.
- 11Marrakech is a city best enjoyed with a little breathing room in the schedule. In my experience, people are warm, welcoming, and eager to accommodate, but plans do not always unfold with perfect rigidity. Tours shift, classes move, and experiences sometimes run on a looser rhythm than expected. The more flexible you are, the better Marrakech tends to feel.
- 12Routes may be limited, seasonal, weather-dependent, or less frequent than expected. Always build your plan around the actual schedule.
- 13It is easy to pack for the fantasy version of the trip: the spontaneous black-tie dinner, the surprise hike, the seven outfit changes in one day. Start with your real itinerary, your actual plans, and the way you truly like to dress when you travel.
- 14Beautiful beaches, charming towns, and an easy family rhythm.
- 15The most convenient restaurant is not always the one worth your appetite and they are often traps.
- 16A neighborhood, beach club, museum, shopping area, boat day, wine tasting, or dinner reservation gives the day shape without making it feel rigid.
- 17A tighter menu usually signals more care from the kitchen.
- 18Your phone is your map, camera, boarding pass, translator, reservation keeper, and emergency lifeline. Keep a charger and portable battery close so you are not the person hunting for an outlet at gate B27.
- 19Start with three colors that work well together and make sense for the destination. This gives your suitcase structure and makes it much easier to mix pieces without creating outfit chaos.
- 20A well-located hotel can save time, taxis, stress, and tired feet. Being able to walk out into the best part of a destination is often worth it.
- 21A suitcase full of “cute pieces” does not always turn into cute outfits. Before anything goes in your bag, make sure it works with at least two other things, fits the actual itinerary, and has a clear reason for coming.
- 22Think polished layers, comfortable shoes, breathable fabrics, and nothing that digs in by hour four.
- 23Book the itinerary that works best for your family, not just the cheapest one.
- 24Carry-on only, checked bag, or both?
- 25It is easy to pack for the fantasy version of the trip: the spontaneous black-tie dinner, the surprise hike, the seven outfit changes in one day. Start with your real itinerary, your actual plans, and the way you truly like to dress when you travel.
- 26Bring clothes for what you will actually do, not just the mood board. Cobblestones, ferries, beach stairs, long lunches, and weather shifts all count.
- 27Do you want beaches, cities, shopping, food, wine, history, scenery, rest, or a little bit of everything?
- 28The best flight outfit feels comfortable but still looks pulled together. Think relaxed trousers, soft knits, matching sets, breathable tees, or a draped jacket instead of anything too tight, stiff, or sloppy.
- 29Photos love definition. A tucked shirt, belted waist, structured dress, tailored trouser, or clean neckline can make an outfit read more polished on camera, even if the pieces themselves are simple.
- 30Bring clothes for what you will actually do, not just the mood board. Cobblestones, ferries, beach stairs, long lunches, and weather shifts all count.
- 31If the plan includes taxis, hotels, rooftops, fine dining, or very short walks, heels may make sense. They can be worth it for the right dinner, wedding, event, or polished city night.
- 32In many places, coffee is meant to be a pause, not a rush.
- 33Cobblestones are not the place for thin, slippery, or overly delicate soles. Look for shoes with structure, grip, and enough cushion to handle uneven streets without making every step feel like a personal challenge.
- 34A tasting, a tour, and a long lunch are not always the same experience and pricing can vary greatly.
- 35If your itinerary is full of cobblestones, hills, old towns, ferries, markets, stairs, or long strolls after dinner, heels may become more burden than benefit. A chic flat, sandal, wedge, or block heel will usually serve you better.
- 36If no one can walk in their shoes, the outfit is already a problem.
- 37A simple palette makes everything work harder. Choose a few core colors, then add one or two accents so your shoes, bags, layers, and accessories can mix easily without creating a suitcase full of almost-outfits.
- 38Private boat days, special meals, wine tastings, beach clubs, guides, or once-in-a-place moments can become the memories of the trip.
- 39Both. Use a credit card for larger purchases and keep some cash for taxis, tips, markets, and smaller local spots.
- 40Tangled jewelry is a vacation mood killer. Use a small jewelry case, pouches, pill organizer, or individual bags so necklaces, earrings, and rings do not become one impossible knot.
- 41The wrong shoes can ruin a beautiful day. Prioritize polished, walkable pairs before adding anything overly delicate.
- 42A beautiful sandal only works if your foot stays in it. For cobblestones, choose ankle straps, slingbacks that actually stay put, supportive flats, fashion sneakers, or sandals with enough coverage to keep you steady.
- 43A beautiful suitcase is less charming when it is heavy before you pack it.
- 44The fastest way to ruin a beautiful afternoon is wearing shoes that cannot handle the walk. Bring pairs that look polished but can survive cobblestones, stairs, airports, and long dinners that somehow turn into long walks home.
- 45Reserve the meals you would be sad to miss. Not every dinner needs to be planned, but the special ones should be.
- 46The right dress can handle sightseeing with flats, lunch with sandals, and dinner with jewelry and a better bag. Look for silhouettes that feel comfortable during the day but still polished enough for evening.
- 47Linen, silk, cotton poplin, knits, raffia, leather, denim, and woven details photograph beautifully because they add depth. Flat fabrics can sometimes disappear, especially in bright light or against busy backgrounds.
- 48Too many transfers can turn a beautiful trip into a luggage relay. Give yourself enough time to actually enjoy each place.
- 49A dream destination in the wrong month can feel crowded, closed, too hot, too cold, or wildly expensive
- 50Anything you truly need should stay with you, not in a checked suitcase. Keep medications, contacts, glasses, and a few essential toiletries in your personal item in case your luggage takes a different vacation.
- 51The best family-friendly stays with space, location, and convenience go quickly.
- 52Do not zigzag across a city or island if you can avoid it. Build days around neighborhoods, regions, or natural routes.
- 53A great mix of long sandy beaches, pretty coves, and flexibility.
- 54Passport, boarding pass, wallet, and hotel confirmation should not be scattered across three bags and a coat pocket.
- 55Beach towns, cities, wine regions, resorts, and countryside escapes each have their own rhythm. Dress for the setting, not just the weather.
- 56Morocco is beautiful, stylish, and sensory in all the best ways, but it is still a country where modest dress is often appreciated, especially around religious sites and in more traditional areas. You do not need to hide yourself, but breezy pieces that cover a bit more tend to feel both respectful and far more comfortable.
- 57The local specialty is usually there for a reason.
- 58A quick coffee at the bar may be priced very differently from table service.
- 59The wrong shoes can ruin a beautiful day. Prioritize polished, walkable pairs before adding anything overly delicate.
- 60Some places offer a few bites. Others give you a full little spread.
- 61Airports are warm, planes are cold, and arrivals can be a completely different season. A light jacket, cardigan, scarf, or wrap gives you options without making the outfit feel bulky.
- 62Snacks, chargers, wipes, and one change of clothes should be easy to grab.
- 63Cream, white, black, navy, tan, denim, and soft gray are the pieces that hold everything together. Your neutrals should work across multiple outfits, not just one very specific look.
- 64What people are actually eating tells you more than the sign outside.
- 65Book the meals that matter, but leave space for the café you stumble into, the wine bar you notice twice, and the place locals keep recommending.
- 66A simple palette makes everything work harder. Choose a few core colors, then add one or two accents so your shoes, bags, layers, and accessories can mix easily without creating a suitcase full of almost-outfits.
- 67A smart suitcase has pieces that work together. Think layers, repeatable shoes, easy accessories, and outfits that can move from day to dinner.
- 68Wear shoes that are comfortable, secure, and easy enough for security without looking like an afterthought. Fashion sneakers, loafers, or sleek flats usually work better than sandals or complicated boots.
- 69Having a plan for arrival makes a big difference after a long travel day.
- 70Every place has its own rhythm. A beach town, wine region, European city, and resort dinner do not ask for the same wardrobe. The goal is not to look like everyone else. It is to look like you understood where you were going.
- 71You don't need a full second wardrobe, but a fresh top, clean underwear, or a simple lightweight outfit can be a lifesaver after an overnight flight, a spill, or a delayed bag.
- 72If heels are coming, keep it to one very versatile pair. They should work with multiple outfits and be comfortable enough to wear for more than twenty minutes outside the hotel room.
- 73The souks are part of the magic, but they are not the place to shop in a rush. One of the biggest mistakes tourists make is accepting the first price, or shopping when they are too overwhelmed to think clearly. Bargaining is expected in Morocco, so a little patience, a little calm, and a little playfulness will usually serve you well.
- 74If you bring height, choose a block heel, wedge, or platform over a skinny heel. Anything that can disappear between stones should probably stay home unless your itinerary involves door-to-door cars and very little walking.
- 75Dining rhythms matter more than most tourists realize.
- 76A little awareness of local habits can make you feel much more in step.
- 77Scenic, relaxed, and full of beaches with easy access and family-friendly amenities.
- 78Do not pack random pieces and hope they become outfits later. Lay everything out by day, activity, or mood so you can see what actually works together before it takes up space in your suitcase.
- 79Smooth spinner wheels matter more than people think.
- 80A smart suitcase has pieces that work together. Think layers, repeatable shoes, easy accessories, and outfits that can move from day to dinner
- 81Not every tour, transfer, upgrade, or ticket needs to be premium. Some days are better left simple.
- 82A little color goes further when it is intentional. Choose one accent, maybe blue, coral, olive, red, butter yellow, or soft pink, and repeat it through a dress, scarf, swimsuit, or bag.
- 83Wine country is much more enjoyable when no one is stressed about driving.
- 84A little distance from the main square often makes a big difference.
- 85A bold earring or special necklace can be enough. Keep the rest simple and versatile so you can dress up outfits without turning your jewelry bag into a second suitcase.
- 86A bank ATM is usually the easiest option. Skip random tourist machines when you can and use one connected to an established bank.
- 87The best vacation photos often happen when your outfit feels connected to the place. Think whites and blues by the water, warm neutrals in old cities, soft earth tones in wine country, or black and cream for a more city-polished look.
- 88Ferries, stairs, docks, taxis, and uneven streets are much easier with a streamlined suitcase.
- 89Phone, headphones, battery pack, camera, Kindle, watch. Future you will be grateful.
- 90Ferries, trains, rental cars, transfers, and domestic flights can shape the whole rhythm of the trip.
- 91Comfort matters, but polished, practical outfits go a long way.
- 92Planes, evenings, and breezy days all call for easy layering.
- 93Some places are best for slow mornings and long lunches. Others reward early starts, full days, and a packed itinerary.
- 94Sunrise walks, long lunches, aperitivo, sunset views, and dinner deserve space. Do not bury the prettiest parts of the day in logistics.
- 95Comfort matters, but it does not have to mean athletic everything. Choose pieces that move well and still look considered.
- 96The best order is usually the local one. Look for regional pasta, seafood, cheeses, pastries, wines, and aperitivo traditions.
- 97Shoes take up the most space, so every pair needs a job. Bring one walkable daytime pair, one polished sandal or flat, and only add a heel if the trip truly calls for it.
- 98Do not pack random pieces and hope they become outfits later. Lay everything out by day, activity, or mood so you can see what actually works together before it takes up space in your suitcase.
- 99Choose the local currency. It usually gives you the better rate.
- 100If the view, timing, comfort, or convenience will not meaningfully change, that is often where you can pull back.
- 101A crowd and a pretty room do not always guarantee a great meal.
- 102Cooking classes, beach clubs, private tours, boat days, wine tastings, and museum tickets are often worth securing ahead.
- 103The chicest travelers are usually not wearing something completely different every day. Bring pieces you love and rewear them in smart ways with different layers, shoes, jewelry, or accessories.
- 104A romantic city weekend, family beach trip, girls’ getaway, and multi-generational vacation all need different things to work beautifully.
- 105Restaurants that know what they do well usually do it better. If they offer everything, they are usually not good at anything.
- 106Do not pack one “perfect” look and hope the trip cooperates. Weather changes, reservations move, and sometimes the best night happens unexpectedly. Bring a few outfits you genuinely love, not one hero look surrounded by backups
- 107Paris, Milan, and New York can make a heel feel useful. Capri, Hvar, Santorini, Venice, and most old European towns may make you regret it quickly. The prettier the street, the less forgiving it usually is.
- 108In busy medina areas, unsolicited directions or sudden “guiding” can turn into an ask for money. It is a classic traveler mistake to assume every friendly approach is purely helpful. Be polite, confident, and clear. If you want help, arrange it intentionally. If you do not, keep moving.
- 109Too many tastings can make the whole experience feel rushed and blurred.
- 110A long flight is already hard enough on an outfit. Choose fabrics that can handle hours of sitting, shifting, and sleeping without looking completely defeated when you land.
- 111A great bag, sunglasses, scarf, hat, belt, or piece of jewelry gives the eye somewhere to land. You do not need a complicated outfit. You need one detail that makes it feel finished.
- 112Look for compression, zip sections, and enough structure to stay organized.
- 113A well-timed snack can prevent half the meltdowns of the day.
- 114Random pieces create overpacking and stressful mornings.
- 115A perfect itinerary is not packed from morning to night. It has time for a second coffee, a better shop, a changed plan, or the view you did not expect.
- 116An island arrival day is not always a full beach day. Leave room for delays, check-in timing, and an easy first dinner.
- 117Let the location influence the palette. Coastal trips love whites, blues, linens, and raffia. Cities can handle black, denim, navy, and polished neutrals. Wine country works beautifully with creams, browns, olives, and soft florals.
- 118Jewelry, belts, scarves, sunglasses, and bags can completely change the feel of an outfit without taking up much room. This is where you get variety without suitcase regret.
- 119Aperitivo is better with a terrace, a piazza, or the right kind of atmosphere.
- 120Boat days, tours, and limited-entry experiences often fill earlier than expected.
- 121Sunglasses, a crossbody, a scarf, a hat, or a beautiful sandal can make simple outfits feel styled without overpacking.
- 122Perfect for families who want beach time with a little adventure built in.
- 123Lip balm, hand sanitizer, gum, headphones, charger, and anything you always dig for the second you sit down.
- 124A food-focused trip should still have room to breathe. Long lunches, slow mornings, and spontaneous snacks are part of the charm.
- 125Think lip balm, hand cream, face mist, eye drops, and anything that helps you feel less like airplane air has personally attacked you. Keep it small, useful, and TSA-friendly.
- 126The chicest travelers are usually not wearing something completely different every day. Bring pieces you love and rewear them in smart ways with different layers, shoes, jewelry, or accessories.
- 127If losing it would ruin the trip, think carefully before bringing it. Travel is full of hotel safes, pool bags, rushed mornings, and tiny bathroom counters. Bring beautiful pieces, but be smart about what is irreplaceable.
- 128Vacation is not the time to discover that your new shoes hate you. Wear them for a real errand day before the trip. If they bother you at home, they will absolutely betray you abroad.
- 129Save hotel addresses, ferry tickets, train tickets, confirmation numbers, and maps in case Wi-Fi gets dramatic.
- 130Enough for the day’s smaller expenses, but not more than you need. Keep the rest secure where you are staying.
- 131Your outfits should match the actual flow of the trip.
- 132Think polished, but practical enough for gravel, grass, stairs, and cellar temperatures.
- 133Know how you are getting from the airport, where you are dropping your bags, and where your first easy meal will be.
- 134“What is the specialty here?” can tell you almost everything.
- 135Shoes are where overpacking goes to thrive. Bring the pairs that match your itinerary, your walking plans, and your actual tolerance for discomfort. If a shoe only works with one outfit, it may not deserve the space.
- 136Outfits photograph better when they move naturally. A dress that catches the breeze, wide-leg pants, a linen shirt, a soft skirt, or a lightweight layer can make a photo feel less posed and more alive.
- 137This is the moment to settle in, sip slowly, and let the evening unfold.
- 138The best travel shoes are the ones that still feel good after museums, markets, lunch, shopping, stairs, and one more “quick walk” that turns into three miles. Style matters, but stamina matters more.
- 139There is no shame in wearing the same trousers, skirt, or dress more than once. The secret is changing the styling, not packing a new outfit for every single moment.
- 140Before you pack it, ask what it goes with. If a piece only works with one exact outfit, it needs to be special enough to earn the space. Otherwise, it may be better left at home.
- 141Never put important jewelry in checked luggage. Keep it with you, ideally in a zipped pocket or small pouch inside your personal item, so it stays close from airport to hotel.
- 142Clear water, beautiful towns, and family-friendly beach options throughout the coast.
- 143A lot of tourist frustration in Marrakech starts with small logistics. Waiting until you are tired, hot, and already late is when you overpay for a ride or make a rushed decision. It helps to sort out your cash, know roughly what a ride should cost, and stay calm about transport rather than negotiating from a place of stress.
- 144Do less on day one and let everyone settle in.
- 145Accessories are not extra when you travel. Sunglasses, a belt, a scarf, jewelry, a beautiful bag, or the right layer can make simple clothes feel intentional. They also take up far less room than another dress you may not wear.
- 146A few well-chosen reservations can make the trip feel far more memorable.
- 147Your travel outfit should work for the first thing you are doing after landing, whether that is checking into a hotel, grabbing lunch, or waiting for your room to be ready. You do not need to be overdressed. You just want to feel human.
- 148Shoes are where overpacking goes to thrive. Bring the pairs that match your itinerary, your walking plans, and your actual tolerance for discomfort. If a shoe only works with one outfit, it may not deserve the space.
- 149Especially if you check bags often or travel internationally.
- 150Some people can wear heels all night. Some people are over it by the lobby. There is no prize for suffering through vacation in the wrong shoes. Pack for the version of yourself who wants to enjoy the evening.
- 151Leave a little room for spontaneity and unexpected favorites.
- 152Long travel days are not the moment to discover your headphones are in your suitcase. Keep headphones, a Kindle, downloaded podcasts, or a small book within reach before you board.
- 153It is worth checking. I also like to travel with more than one card and keep a third loaded into Apple Pay as a backup, even if I do not bring it physically.
- 154Make sure it is comfortable for your stride and body.
- 155Airline meals, airport lines, and tight connections are not always kind. A few good snacks, gum, and an empty refillable water bottle can make the whole day feel more civilized.
- 156The best trips usually come with something you want to bring home: wine, ceramics, linen, perfume, a sweater you did not plan on buying but absolutely needed. Leave a little space so shopping feels fun, not like a suitcase crisis.
- 157Airports, train stations, rental car desks, ferries, and families all have a way of humbling a tight schedule.
- 158An easy, classic family beach trip with calm water and practical amenities.
- 159The best trips usually come with something you want to bring home: wine, ceramics, linen, perfume, a sweater you did not plan on buying but absolutely needed. Leave a little space so shopping feels fun, not like a suitcase crisis.
- 160Choose luggage you can actually store when you are home.
- 161Anything expensive, sentimental, or hard to replace belongs with you. Jewelry, designer sunglasses, camera gear, and important tech should never be checked.
- 162City hopping, train travel, short trips, Europe, and anyone who hates waiting at baggage claim.
- 163Planes, trains, and airports have their own climate system. A cashmere wrap, scarf, cardigan, or light jacket can double as warmth, a pillow, or a way to look a little more pulled together when you land.
- 164Longer stays, winter trips, family travel, special events, and trips where shopping is part of the plan.
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